1-(6-azidohexyl)-5-methyl-1H-pyrimidine-2,4-dione | 823226-71-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(6-azidohexyl)-5-methyl-1H-pyrimidine-2,4-dione
• 英文别名: 1-(6-azidohexyl)-thymine；1-(6-Azidohexyl)-5-methylpyrimidine-2,4(1H,3H)-dione；1-(6-azidohexyl)-5-methylpyrimidine-2,4-dione
• CAS: 823226-71-7
• 化学式: C₁₁H₁₇N₅O₂
• 分子量: 251.288
• InChiKey: RNPATFAQWWOVRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(6-azidohexyl)-5-methyl-1H-pyrimidine-2,4-dione 、 5,5''-diethynyl-2,2':5',2''-terthiophene 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以89%的产率得到1,1'-(([2,2':5',2''-terthiophene]-5,5''-diylbis(1H-1,2,3-triazole-4,1-diyl))bis(hexane-6,1-diyl))bis(5-methylpyrimidine-2,4(1H,3H)-dione)
  参考文献：
  名称：

  通过“点击”反应进行端基远螯寡聚和聚噻吩的合成：通过LC-ESI-TOF MS进行合成和分析

  摘要：

  从远螯炔炔官能化的P3HT经由铜（I）催化的叠氮化物/炔“点击”反应开始，制备了具有复杂氢键基团的端基改性聚（3-己基噻吩）（P3HT）。预计最终的聚合物将排列成由交替的供体/受体聚合物组成的假嵌段共聚物，用于太阳能电池材料中。从溴-telechelic P3HT（M n = 2000 g / mol; M w / M n＝ 1.2）通过McCullough方法制备，随后进行额外的溴化反应，得到具有（80％Br / Br； 20％H / Br）端基的远螯P3HT，通过Sonogashira偶联制备了相应的α，ω-（三甲基甲硅烷基）乙炔基-P3HT。反应。首次使用LC-ESI-TOF方法对炔基-telechelic P3HT物种的端基进行了分析，证明形成了〜59％（乙炔基/乙炔基）和〜40％（乙炔基/ H）物种在α，ω-（三甲基甲硅烷基）乙炔基-P3HTs中，只有少量（〜1％）的相应（H /

  DOI：

  10.1021/ma1016727

文献信息

• End-Group Telechelic Oligo- and Polythiophenes by “Click” Reactions: Synthesis and Analysis via LC-ESI-TOF MS
  作者：Claudia Enders、Susanne Tanner、Wolfgang H. Binder

  DOI：10.1021/ma1016727

  日期：2010.10.26

  respective (H/H)-modified species. Additionally, MALDI methods were used for a qualitative assessment. Subsequent azide/alkyne “click” reaction with either 1-(6-azidohexyl)thymine or 5-((4-azidobenzoyl)amino)-N,N′-(6-(octanoylamino)pyridin-2-yl)isophthalamide using CuI, CuBr(PPh3)3, or CuI·P(OEt)3 as catalyst yielded the final products with attached hydrogen bonds as judged by LC-ESI-TOF methods. The described

  从远螯炔炔官能化的P3HT经由铜（I）催化的叠氮化物/炔“点击”反应开始，制备了具有复杂氢键基团的端基改性聚（3-己基噻吩）（P3HT）。预计最终的聚合物将排列成由交替的供体/受体聚合物组成的假嵌段共聚物，用于太阳能电池材料中。从溴-telechelic P3HT（M n = 2000 g / mol; M w / M n＝ 1.2）通过McCullough方法制备，随后进行额外的溴化反应，得到具有（80％Br / Br； 20％H / Br）端基的远螯P3HT，通过Sonogashira偶联制备了相应的α，ω-（三甲基甲硅烷基）乙炔基-P3HT。反应。首次使用LC-ESI-TOF方法对炔基-telechelic P3HT物种的端基进行了分析，证明形成了〜59％（乙炔基/乙炔基）和〜40％（乙炔基/ H）物种在α，ω-（三甲基甲硅烷基）乙炔基-P3HTs中，只有少量（〜1％）的相应（H /
• Combining Ring-Opening Metathesis Polymerization (ROMP) with Sharpless-Type “Click” Reactions: An Easy Method for the Preparation of Side Chain Functionalized Poly(oxynorbornenes)
  作者：Wolfgang H. Binder、Christian Kluger

  DOI：10.1021/ma0480087

  日期：2004.12.1

  ROMP yielding the final polymers; (b) the ROMP polymerization furnishing first poly(oxynorbornenes) bearing acetylenic and azido moieties and subsequently attaching the functional units by use of the “click” reactions onto the modified polymers. Both strategies show efficient functionalization behavior with a high tolerance of functional groups with respect to the functional units attached as demonstrated

  叠氮化物和乙炔之间的无尖锐的1,3-偶极环加成反应（“点击反应”）用于制备侧链内的功能性聚氧降冰片烯。应用了两种不同的策略将ROMP聚合物的制备方法与1,3-偶极环加成反应相结合：（a）通过1,3-偶极环加成反应将官能团（即疏水和氢键合单元）与7-带有乙炔的氧降冰片烯和随后的ROMP产生最终聚合物；（b）通过ROMP聚合反应，首先提供带有炔和叠氮基部分的聚（氧降冰片烯），然后通过“点击”反应将官能团连接到改性聚合物上。1 H和13 C NMR光谱学开辟了仅使用很少的原料制备多种官能化聚氧降冰片烯的可能性。
• Surface-modified nanoparticles via thermal and Cu(<scp>i</scp>)-mediated “click” chemistry: Generation of luminescent CdSe nanoparticles with polar ligands guiding supramolecular recognition
  作者：Wolfgang H. Binder、Robert Sachsenhofer、Christoph J. Straif、Ronald Zirbs

  DOI：10.1039/b618510j

  日期：——

  A new, simple and highly versatile method for the surface modification of luminescent cadmium selenide nanoparticles (CdSe NPs) based on 1,3-dipolar cycloaddition reactions is described. Uniform, trioctylphosphine oxide (TOPO)-covered CdSe NPs were prepared and subjected to two ligand-exchange reactions: first, ligand exchange was accomplished with pyridine, fully removing the TOPO ligand from the CdSe surface. In a second step, either 1-[(3-azidopropyl)octylphosphinoyl]octane or hex-5-ynoic acid 3-(dioctylphosphinoyl)propyl ester were added, attaching an azido or an acetylene moiety to the NP surface. Further thermal or Cu(I)-mediated 1,3-dipolar cycloaddition reactions on the residual azido/acetylene moieties with a variety of acetylenes/azides furnished the modified CdSe NPs with supramolecular receptors (i.e. barbituric acid, thymine, oligoethyleneglycol) on their surface. Photoluminescence measurements reveal a ∼50% residual quantum yield (relative to TOPO-covered CdSe NPs) after ligand modification, thus presenting an efficient pathway towards luminescent, surface modified CdSe NPs. The presence of the different functional groups was proven by 1H-NMR, 31P-NMR spectroscopy and by use of a nanoparticle-bound spiropyran dye and subsequent fluorescence quenching experiments. In order to further exploit the ligands on the CdSe NP surfaces, supramolecular recognition via binding to self-assembled monolayers (SAMs) presenting the matching receptor was investigated, leading to dense layers of CdSe NPs on planar surfaces as verified by AFM measurements. The concept offers a simple method for guiding the binding and recognition of luminescent CdSe NPs and related NPs onto surfaces.

  本文描述了一种基于1,3-偶极环加成反应的新型、简单且高度通用的发光硒化镉纳米粒子（CdSe NPs）表面改性方法。制备了均匀的三辛基氧化膦（TOPO）覆盖的CdSe NPs，并使其发生两次配体交换反应：首先，用吡啶完成配体交换，完全去除CdSe表面上的TOPO配体。第二步，加入1-[(3-叠氮丙基)辛基膦酰]辛烷或己-5-炔酸3-(二辛基膦酰)丙酯，将叠氮或乙炔部分连接到NP表面。在残留的叠氮/乙炔部分上进一步发生热或Cu(I)介导的1,3-偶极环加成反应，与各种乙炔/叠氮反应，使改性CdSe NPs表面具有超分子受体（即巴比妥酸、胸腺嘧啶、寡乙二醇）。光致发光测量显示，配体改性后残留量子产率为50%以下（相对于TOPO覆盖的CdSe NPs），从而为发光、表面改性的CdSe NPs提供了有效途径。1H-NMR、31P-NMR光谱以及纳米粒子结合螺吡喃染料和随后的荧光淬灭实验证明了不同
• Hydrogen-bonded perylene/terthiophene-materials: synthesis and spectroscopic properties
  作者：Ali Shaygan Nia、Claudia Enders、Wolfgang H. Binder

  DOI：10.1016/j.tet.2011.10.096

  日期：2012.1

  The synthesis of layered donor/acceptor-materials based on perylenes (1a-c) and ter(thiophen)es (2a, 2b), ordered by hydrogen bonding moieties is reported. Based on the successful (selective) chlorination of 3,4:9,10-perylene tetracarboxylic dianhydride (3) to obtain a perylene derivative with only four chlorine atoms, subsequent functionalization with different hydrogen-bonding moieties is achieved via the azide/alkyne click reaction as proven by extensive ESI-TOF measurements. The perylene- (la-c) and terthiophene- (2a, 2b) compounds are useful as acceptor and donor parts, respectively, in organic solar cells as proven via UV vis and fluorescence measurements. Charge transfer between donor and acceptor parts (2a/1b) was determined as 41% via fluorescence resonance energy transfer (FRET), proving the association of the two components via the attached hydrogen bonding moieties. These measurements indicate that the mixture 2a/1b displays large potential for use as a layered ordered material with controlled spacings for organic solar cells based on a thereby facilitated charge-transfer. (C) 2011 Elsevier Ltd. All rights reserved.